All Forum Posts by: Joshua Tucker

I know pricing tools can be frustrating, but they might be worth another shot. Sometimes it just takes tweaking them over time to see results. You could also focus on attracting weekday guests—maybe offer discounts for longer stays or highlight features like fast Wi-Fi or a comfy workspace to appeal to remote workers.

Since a hot tub isn’t an option, maybe think about other ways to stand out. Could you lean into local experiences or create a unique theme for your listing? Something that makes guests feel like they’re getting more than just a place to stay. Partnering with nearby businesses could also help—like offering discounts at local restaurants or attractions.

And don’t underestimate the power of a great listing description. Keep playing around with keywords to make it pop in searches. Adding some social media marketing could also be a game-changer—targeting weekend tourists or traveling professionals with ads.

You’re doing a lot right.

It sounds like you're being really strategic here, which is smart. A self-directed IRA could be a good way to defer taxes, but there are some rules to keep in mind—like keeping all the income in the IRA until retirement. Another angle might be looking at how the profits are classified. Since this is a short-term flip, the IRS usually sees it as active income, but if your role is truly hands-off, there might be a way to treat it differently.

Have you thought about how you're structuring the deal? Sometimes using an LLC or similar setup can change how the income is taxed. And while a 1031 exchange isn't an option, some people explore alternatives like installment sales to spread out taxes or even tweaking the investment structure so your returns are treated as interest instead of equity.

There are definitely some creative strategies out there.

Makes sense. Thanks 

What specific tax benefits can high net worth individuals receive from building real estate on tribal land?

Hello @Lacey A.,

Renting your primary home back to yourself isn’t typically allowed by the IRS for tax purposes, even if structured through an LLC. The IRS views this as a related-party transaction, and deductions like rent paid to yourself wouldn’t qualify. You might consider other strategies, like taking a home equity loan or refinancing to fund repairs, but consulting with a tax professional or CPA would be the best next step for your specific situation.

Hope this helps!

The rent-to-price ratio is a quick way to measure if a property might cash flow. You just divide the monthly rent by the purchase price. For example, if a property rents for $2,000 and costs $200,000, that’s a 1% rent-to-price ratio ($2,000 ÷ $200,000). Ratios like 0.7% or 0.8% can still work, but it depends on your market and expenses. Hope that clears it up!

Your calculation’s close, but cash-on-cash return is usually about cash flow, not appreciation. What you’re calculating is more like a return on equity (ROE). That 95% makes sense as an appreciation return, but for true CoC, you’d need rent income factored in.

You’re absolutely right. Building a portfolio and scaling smart can eventually replace your income, but it’s not as simple as podcasts make it seem. Cash flow is tricky, especially early on, because so much of it gets eaten up by repairs, vacancies, and reserves.

That said, some asset classes—like laundromats—can provide more immediate cash flow if structured well. They’re a different kind of play than rentals but can complement long-term holds by creating steady income streams without waiting for a portfolio to mature.

Flipping is another great option, especially if you’re looking for chunks of capital to reinvest, but it’s a different game with higher risk and shorter timelines. A lot of investors I know mix strategies: flips, cash-flowing assets, and long-term holds to get that balance of growth and income.

It really comes down to what fits your goals and risk tolerance. Thoughts?